If you’re going to get anywhere near Don Stewart, be warned: The man’s about to make fun of you.

Don’t worry. He’s an equal opportunity tease, and he saves his sharpest barbs for himself. Take his comment to one of his riders after the ASPCA Maclay Region 3 qualifier. That rider forgot the final fence in the test at the competition, and Stewart reacted by telling the rider (and her mother) “I was so excited. Then your mother’s genes kicked in.”

That’s the sort of taunt that out of context might sound, at best, unkind. But when it’s delivered in Stewart’s lilting North Carolina accent with a big smile and an easy laugh, it produces just the sort of levity that transforms the day of a major equitation class from a stressful experience to a manageable one. And if training or co-training three of eight winners at ASPCA Maclay Regional qualifiers is any indication, that style produces results.

“He definitely knows that all of us get nervous,” Meg O’Mara said to me when we chatted after her win in Region 3 for a story in our Oct. 8 issue. “He’s really focused, but then he’ll crack a joke and make us laugh. He calms us down.”

All three of those winners independently described Stewart as the funniest guy they’d ever met, which suits him just fine. It’s part of a larger goal to teach teenagers more than how to counter-canter through a tight corner.

“I want to teach the kids to laugh and to learn to laugh at themselves,” he said. “It’s an important life lesson that they need to learn. I try to downplay the importance of the regionals or finals or wherever we are. I tell them that this isn’t going to be a cure for cancer, and 10 years from now you’re going to laugh at yourself about how stressed you are. It’s just another life lesson, and you have to keep it in perspective. The key with us is to keep it a little lighter than some and a positive experience.”

As light as Stewart keeps things with his students, it’s not all fun and games. He trains and co-trains plenty of top riders, and he has a knack for being able to evaluate horses and riders as individuals. He and his team tailor programs to fit each one. That’s not an easy feat when at an average show this summer he’d have upwards of 25 juniors, alone, from across the country and 70 horses in training.

Besides his three winners at regionals, the Ocala, Fla., trainer had another six students who qualified from Region 5, and another six from Region 3. And, as he put it, “I’ll be holding some Californians' hands when we get to finals.” Stewart has a cadre of regular students and also a long list that he meets up with at major competitions.

He’s quick to give credit to other trainers and parents who contributed to wins, including Mary Babick who worked with O’Mara, Sherry Templin who regularly trains region 6 winner Jeffery Tolson, and Brandie Holloway who keeps her daughter, region 5 winner Hunter Holloway, in line at home. He’s honest with his criticism but defensive of his students in the face of perceived unfairness. And the kids, new to his program and old, all seem to really enjoy it.

Stewart’s also not afraid to give a rider with raw talent and a solid foundation a chance. After seeing Tolson ride on the HITS Thermal circuit, he called up Templin and asked about his attitude in the barn, noting, “If the work ethic’s not there, it’s not worth messing with.” Templin assured Stewart that the Arizona-based rider had the drive and didn’t know the word lazy. So Stewart invited him to check out the East Coast show scene as a working student, an experience which left him beyond inspired.

“I could spend all day at the ring watching him train horses,” said Tolson. “He has so many tricks for each horse—it’s amazing how his mind works. It was really interesting to learn from him.”

Stewart has students of all ages, but he has a special way with the teenagers. For him, understanding where his students are coming from is part of the key to bringing out the best in them.

“In my lifetime we’re seeing this huge societal change, and not just in the horse business,” he said. “Things are just more relaxed. [The horse world used to be from] a more military-type background, and now that’s changing and more relaxed. I try not to keep it quite as rigid. I want the kids to enjoy what they did and know that it’s a learning process. It’s always really important not to humiliate or embarrass them in front of their friends.”

I can’t remember another trainer, equitation specialist or not, intuiting and acknowledging the unique challenges of training riders of this age the way Stewart does. After all, so many of these riders have taken on responsibilities far beyond their years and have exceptional drive and focus to excel at the sport. It’s easy to forget that at the end of the day, these elite athletes are still learning to drive, bumbling through changing social lives and turning in research papers. A competitive show environment isn’t necessarily a supportive one for what can be a tough period in life. The kids I talked to all described the environment at Don Stewart Stables as overwhelmingly positive.

O’Mara saved a text from a new recruit to the barn, who wrote to her saying she never knew there could be so many nice people who ride well at one barn.

“We don’t get competitive with each other,” said O’Mara. “Yesterday the judges were right behind us, and Geoff [Hesslink] turned to Hasbrouck [Donovan] and said, ‘How many [strides] are you going to do?’, and she had to shush him. We’re just all so used to talking and goofing around together.”